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(Diethylamino)sulfur trifluoride → N-(3-(3,6-dibromo-9H-carbazol-9-yl)-2-fluoropropyl)-3-methoxyaniline

HRID 922139
Notes
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Reaction equation

HRID 922139 reaction equation
CCN(S(F)(F)[F:7])CC.[Br:10][C:11]1[CH:12]=[CH:13][C:14]2[N:15]([CH2:25][CH:26](O)[CH2:27][NH:28][C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[CH:30]=3)[C:16]3[C:21]([C:22]=2[CH:23]=1)=[CH:20][C:19]([Br:24])=[CH:18][CH:17]=3>C(Cl)Cl>[Br:10][C:11]1[CH:12]=[CH:13][C:14]2[N:15]([CH2:25][CH:26]([F:7])[CH2:27][NH:28][C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[CH:30]=3)[C:16]3[C:21]([C:22]=2[CH:23]=1)=[CH:20][C:19]([Br:24])=[CH:18][CH:17]=3
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 3103961P7C3-OMe

Product 1

HCID 46853447N-(3-(3,6-dibromo-9H-carbazol-9-yl)-2-fluoropropyl)-3-methoxyanilineYield 5.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

DAST [(Et2NSF3) 0.12 ml, 0.916 mmol] was added dropwise to a solution of 1-(3,6-dibromo-9H-carbazol-9-yl)-3-(3-methoxyphenylamino)propan-2-ol (0.102 g, 0.203 mmol) in 6.0 ml of anhydrous DCM at −78° C. The reaction was stirred at −78° C. for one hour before being slowly warmed to 0° C. over 5 hours. The reaction was quenched by addition of phosphate buffer (pH=8) and extracted with DCM. The aqueous phase was extracted twice with 10 ml DCM. The combined organics were dried over Na2SO4, filtered and concentrated. The crude reaction material was purified by flash chromatography on SiO2 (20% EtOAc/hexanes/0.2% TEA). Fractions containing the desired fluorinated product were further purified with 40% EtOAc/hexanes (+0.1% TEA). Isolated 5.7 mg desired product.

Workup

  1. temperaturebefore being slowly warmed to 0° C. over 5 hours
  2. customThe reaction was quenched by addition of phosphate buffer (pH=8)
  3. extractionextracted with DCM
  4. extractionThe aqueous phase was extracted twice with 10 ml DCM
  5. dry with materialThe combined organics were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude reaction material
  9. customwas purified by flash chromatography on SiO2 (20% EtOAc/hexanes/0.2% TEA)
  10. additionFractions containing the
  11. customwere further purified with 40% EtOAc/hexanes (+0.1% TEA)

Sources & evidence

ORD record
ord-51fb6e00f52a4090898baf9e549c9128
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09278923B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes